On price
1. What is the monthly figure if I pay monthly? Almost every published price is the annual one. The monthly figure is often 30 to 80 percent higher. Ask for both and decide against the one you will actually pay.
2. What is the minimum number of seats or licenses? Some providers will not sell you fewer than three. If you are one person, that turns a thirty dollar plan into a ninety dollar bill before anything else is added.
3. What is on the first invoice that is not on the pricing page? Card processing fees, regulatory cost recovery fees, taxes, one-time setup charges, number porting charges. Ask for a sample first invoice for your configuration. Ours carries a 2.75% card processing fee and a 3% regulatory fee plus applicable taxes, and we put that on the pricing page rather than in a footnote.
4. Which of the things I just saw demonstrated are add-ons? Toll-free numbers, unlimited domestic minutes, analytics, call recording, extra meeting capacity and AI features are commonly priced separately. Price the configuration you would actually run.
On the contract
5. What is the minimum term, and what happens if I leave early? Some providers quote their best rates only against a twelve-month agreement, and some charge early termination fees up to the full remaining contract value. Month to month costs more per month and is worth it if you are not certain.
6. Can I try it myself, today, without talking to anyone? A self-serve trial tells you something a demo cannot, because a demo shows you what somebody else chose to show you, on their data, at their pace.
7. Is texting switched on during the trial? This is the one to check. At least one major provider's trial terms state that SMS is not available for trial use, which means you cannot test the feature most small businesses care about most.
On the things that break
8. Who answers when something goes wrong, and on which plan? Phone support is frequently a higher tier. When the phone system is the thing that is broken, email support is an uncomfortable place to be.
9. What happens to my calls when my internet goes down? The honest answer is that calls to your number keep arriving and can be routed to mobiles automatically, while desk phones in the affected building stop working. Be wary of anyone who answers this by claiming it cannot happen.
10. Can you evidence your uptime figure? Published availability numbers are often marketing copy rather than measurement. A provider who can point to a status page with history is telling you something. One who quotes a number with nothing behind it is not.
On getting out again
11. Can I take my number with me? Number portability is a legal right in the United States, but the experience varies. Ask how long it takes, what it costs, and whether they charge to release a number. Ask before you sign, not when you are leaving.
12. What happens to my recordings, voicemails and transcripts if I cancel? Many providers delete them, sometimes immediately. Ours are permanently deleted if a trial lapses without converting, and we say so in the terms rather than in a support article.